While the precise origin of the pirate flag is
unknown, its ancestry can be traced with some certainty. They were used to
intimidate the enemy or victim, and the flag was designed to conjure up fear and
dread. It was an important part of the pirate armory, and was the pirate's best
form of psychological warfare, especially when combined with a preceding
reputation of not showing any quarter if opposed. If a pirate could intimidate
an enemy to heave-to without offering resistance, then danger to the pirate crew
would be eliminated, and the victim's ship could be taken undamaged, thus
maintaining its value. Threatening images on the flag were often associated with
a known pirate (and hence his reputation), or could conjure up more specific
warnings. For example, Bartholomew Roberts bore a grudge against the island
colonies of Barbados and Martinique, so in their waters he used a flag showing a
pirate figure (presumably Roberts himself) standing on two skulls. Under one
were the letters 'ABH' (standing for 'A Barbadian's Head'), and under the other
was 'AMH' (for 'A Martiniquan's Head'). The threat was clear and sailors from
those colonies would expect no mercy if they offered any resistance.

Identifying an enemy at sea has always been a
difficulty business. In the 16th century, royal ships painted their
sails with national emblems (e.g. Tudor Roses for English vessels, Catholic
crosses for Spanish ones), but these ships operated in distinctive naval
squadrons, treasure 'flotas' or other armada like forces. For other
vessels, no such symbols were used. Instead, national flags or banners were
employed, an identification technique first used in the medieval period. By the
17th and 18th centuries, national symbolism had stabilized
enough for publishers to be able to produce flag identification charts, listing
the flags of all known maritime nations.

At sea, these symbols indicated national
identity, and whether the vessel was potentially friendly or hostile, although
this was not always a reliable indication. Privateers or pirates (as well as
national warships) often used foreign flags and banners, in order to entice the
enemy within range. As long as these flags were replaced with the appropriate
national emblem, this was seen as a legitimate ruse de guerre. The best
policy was usually to assume all ships were hostile, especially in time of war.

Privateers, approved as such by their national
governments, flew their respective national flag (e.g. the cross of St. George,
or, after 1707, the union jack for England or the Dutch Tricolor for Holland.)
By the mid 17th-century, privateers flew privateering symbols in
addition to national flags. Without the national flag, they would have been
considered as pirates. Although the nature of these early privateering flags is
unrecorded, in 1694, an English Admiralty law made the flying of a red
privateering flag mandatory for English Privateers. The red flag is depicted in
earlier Dutch paintings, but the meaning was not recorded. The red flag today is
associated with warning, and in the context of late 17th century
privateering, it served the same purpose of warning another vessel not to
resist. The flag as defined by the Admiralty in 1694 was an all red flag known
as 'The Red Jack'. It's description as 'that recognized privateering symbol'
indicated that the device was flown earlier in the century. Privateers later
referred to 'sailing under the Red Jack'. At around the same time, a new symbol
appeared. References to a black flag were noted in reports of privateering
actions, the first in 1697. This was raised by a privateer if the victim's
vessel showed any kind of resistance, and was a symbol that little or no quarter
would be given. Yellow flags were also mentioned, although unlike their current
association with quarantine, their precise meaning in the late 17th
century was unknown. Therefore, by 1700, red and black were flag colors
associated with privateering. When the outlets for legitimate privateering dried
up at the end of the War of the Spanish Succession in 1714, many privateers
turned to piracy. They simply retained their old symbols, although black became
the favored color. Red continued to be associated with privateering until the 19th
century. The American 18th century privateering color of a red flag
overlaid with white horizontal stripes provided the inspiration for part of the
existing flag of the USA. Some reports say the Jolly Roger was run up first, to
signify an offer of quarter. If the victim refused to surrender, the plain red
flag was flown to show the offer had been withdrawn and no mercy could be
expected.

The use of the term 'Jolly Roger' was not a
Hollywood myth, and is derived from a couple of sources. The French name for the
privateering red flag was the Jolie Rouge (Jolly Red), and this was said
to have been converted into 'Jolly Roger'. Another possible derivation comes
from the word 'Roger'. In late 17th century England the word 'rouge'
was used in association with the rogue laws, limiting vagrancy in England.
'Roger' sprang from this, and was used as a slang word for a vagabond, beggar or
vagrant. The privateering association with 'Sea Beggars' goes back to the phrase
used by Dutch privateers (and freedom fighters) in the late 16th
century. It continued the be used as a romanticized description of privateers
operating in the English Channel, particularly those from the port of Dunkirk.
The 'Jolly Roger' described the privateering symbol, whether a red or black
flag. It later changed from the description of a privateering symbol to a
piratical one. Yet another possibility come from the fact that the devil was
sometimes referred to as 'Old Roger', so the flag suggested the wrath of the
devil.

In popular legend, every pirate flag displayed
a skull above crossed bones or crossed swords. In fact there was ample
variation, since every crew wanted a unique flag. The first reference to a
modified basic 'Jolly Roger' was in 1700, when the French privateer Emmanuelle
Wynne flew a black flag embellished with a skull, crossed bones and an hourglass
(Henry Every flew a basic skull and crossed bones, though with the skull turned
to the side, as early as 1696, on both a red and black flag). It was presumably
also used before the turn of the century, although there is no surviving
evidence. It may also have indicated that the flyer no longer considered himself
to be a privateer, and was a full-blown pirate. What is known is that following
1700, additional emblems on the basic red or black flag were increasingly
associated with piracy, and different symbols were in turn associated with
individual pirate captains.

Of these, the most common symbol was the
skull, the symbol of death. It was also frequently depicted in association with
crossed bones, another death symbol (although only Edward England flew the
"skull and crossed bones" in it's pure form. Christopher Condent's
banner repeated the same symbol 3 times.) Both signs were commonly 'momento mori'
on 16th and 17th century gravestones all over the British
Isles. Other symbols were complete skeletons, spears, swords, hourglasses,
initials, hearts, crossed swords, wings and raised glasses. In an era where
symbolism in art and everyday life was commonplace, each had a distinct and
immediately recognizable meaning. Apart from the death association with bones,
skeletons and skulls, dancing skeletons meant dancing a jig with death, a
fatalistic reference the flyer didn't care about his fate. This was also the
origin of the raised glass symbol ('toasting death'). Weapons were a portent of
slaughter to come, while hourglasses and wings indicated that time was running
out (or flying away). All these symbols can be found in contemporary allegorical
paintings of death, or on gravestones.

The symbols were often combined. For instance,
Christopher Moody used a skull and crossed bones, a raised sword and a winged
hourglass. Edward Teach ('Blackbeard') flew a flag depicting a horned skeleton
holding an hourglass and a spear next to a bleeding heart. In addition to his 'ABH/AMH'
flag, Bartholomew Roberts also flew one depicting a pirate holding an hourglass,
alongside a skeleton clutching a spear. The fatalism in pirate symbolism was
evident, and it probably applied to pirates as well as their victims.

National flags were still flown, often in an
attempt to show that the pirates still wanted to be seen as privateers who only
attacked the ships of other nations. If the countries were at peace, or if the
pirate held no privateering commission, this meant little or nothing. In 1718
Charles Vane flew the English flag from one mast and a black pirate flag from
another. In 1720, Edward England flew a black flag from his mainmast, a red flag
from his foremast and the English flag from his ensign staff!

Jolly Rogers were rough and ready affairs, run
up by a pirate ship's sail maker or any member of the crew who was handy with a
needle. Many Nassau pirates had their flags made for them by a sail maker's
widow, who accepted payment in brandy.